Structure determination and quantification of a new flavone glycoside with anti-acetylcholinesterase activity from the herbs of Elsholtzia ciliata

Three acacetin triglycosides (compounds 1, 2 and 3) were isolated from the herbs of Elsholtzia ciliata (Labiatae). The structure were identified as 7-O-β-D-glucopyranosyl-(1 → 2)[α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranoside (compound 1), 7-O-(6-O-acetyl)-β-D-glucopyranosyl-(1 → 2)[α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranoside (compound 2) and 7-O-(6-O-acetyl)-β-D-glucopyranosyl-(1 → 2)[(4-O-acetyl)-α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranoside (compound 3) of acacetin. The structures of these compounds were determined on the basis of 2D-NMR spectroscopic data. Compound 3 has not been isolated from a natural source. In addition, the three compounds were quantitatively analysed by HPLC. Acetylcholinesterase (AChE) inhibition activity was assayed to find anti-Alzheimer’s activity, since this enzyme increases the concentration of acetylcholine (ACh), a neurotransmitter, responsible for brain’s memory. Acacetin, the aglycone of the three compounds, exhibited a potent anti-cholinesterase activity (IC₅₀, 50.33 ± 0.87), though its glycosides (1, 2 and 3) were less active. HPLC analysis demonstrated that the three compounds were contained in the MeOH extract in the order of compounds 2 (12.63 mg/g extract) > 3 (3.10 mg/g) > 1 (2.92 mg/g).     

Energetics of flavone and flavanone

In this work, we have determined the experimental standard (p° = 0.1 MPa) molar enthalpies of formation, in gas phase, of flavone and flavanone.These results were obtained by combining the standard molar enthalpies of formation in the condensed phase with the standard molar enthalpies of sublimation. The former values were derived from combustion experiments in oxygen, at T = 298.15 K, in a static bomb calorimeter. The values of the standard molar enthalpies of sublimation were obtained by Calvet microcalorimetry and corrected to T = 298.15 K.High-level density functional theory calculations using the B3LYP hybrid exchange–correlation energy functional with extended basis sets and more accurate correlated computational techniques of the MCCM/3 suite have been performed for the compounds.The obtained results, experimental and computational, for flavone and flavanone were compared with those obtained for chromone and chromanone, respectively.     

The interpretation of the NMR spectra of flavone C-monoglycosides

Chemistry of Natural Compounds - 1. A satisfactory explanation of the structures of orientin and homoorientin has been obtained in an evaluation of the results of NMR spectroscopy from the point of...     

Structures of flavone and flavonol glycosides

Summary Literature information on the structures of O-glycosides of flavones and flavonols has been generalized. Using the methods of combinatorial mathematics, the possibility of a great diversity of the structure of the glycosides has been shown without taking into account their acylation, the dimensions of the oxide rings of the sugars, and the nature of the glycosidic bonds.Pyatigorsk Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 413–425, July–August, 1972.     

New flavone glycoside fromScutellaria ramosissima

Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 317–318, March-April, 1995. Original article submitted November 7, 1994.     

Thiazole analogs of chalcone and flavone

New thiazole analogs of chalcones and their epoxides were obtained. Thiazole analogs of flavone and isoflavone were synthesized for the first time on the basis of these compounds. It is shown that o-hydroxyphenylpyrazole derivatives are formed by the action of hydrazine hydrate on 2-(4-thiazolyl)chromones. The PMR spectra of the new substances are presented and discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1202–1208, September, 1981.     

New acylated flavone glycoside fromGnaphalium uliginosum

A new acylated flavone glycoside has been isolated for the first time from the herb marsh cudweed, and for it the structure of 6-caffeyl-7--D-glucopyranosyloxy-4,5-dihydroxy-3,6dimethoxyflavone has been established. In addition, the aglycone, identified as 4,5,7-trihydroxy-3,6-dimethoxyflavone has been isolated. The identifications were made on the basis of UV, IR, PMR, and mass spectra, the products of alkaline and acid hydrolyses, and the results of elementary analysis, melting points, and specific rotations.Vitebsk Medical Institute. All-Union Scientific-Research Institute of Medicinal Plants, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 311–315, May–June, 1979.     

Fully and partially fluorinated flavone derivatives

In the crystal structures of the fully and partially fluorinated flavone derivatives 5,6,7,8‐tetrafluoro‐2‐(2,3,4,5,6‐pentafluorophenyl)‐4H‐1‐benzopyran‐4‐one, C₁₅HF₉O₂, (I), and 5,6,7,8‐tetrafluoro‐2‐phenyl‐4H‐1‐benzopyran‐4‐one, C₁₅H₆F₄O₂, (II), the pentafluorophenyl group and the pyranone moiety in (I) are twisted due to repulsion of the F substituents, and a CO(δ⁻)...π(δ⁺) intermolecular interaction is observed between the carbonyl O atom and the pentafluorophenyl group. In (II), on the other hand, the phenyl group and the pyranone moiety are almost coplanar, and arene–perfluoroarene interactions are observed in the head‐to‐tail intermolecular columnar stacking between the phenyl group and the tetrafluorophenylene moiety.     

New acetylated flavone C-glycosides from Iris lactea

Chemical investigation of the aerial parts of Iris lactea afforded three new flavone C-glycosides including 4?-O-acetyl-embinin (1), 2?,4?-O-diacetyl-embinin (2) and 6″,4?-O-diacetyl-embinin (3) along with the known analogue embinin (4). Their structures were elucidated by 1D and 2D NMR spectroscopic analysis as well as by HRESIMS data. The sugars were characterized following acid hydrolysis of the respective glycosides and TLC analysis compared to known standards. Duplicated signals can be observed in the NMR spectra, indicating the presence of rotamers caused by rotational hindrance around the glycosyl-flavone CC linkage. All isolated compounds were tested for their antimicrobial and cytotoxic activities but found to be inactive.     

A new flavone glucoside from Stachys aegyptiaca

In addition to 5,7,3′-trihydroxy-6,4′-dimethoxyflavone, 5,7,3′-trihydroxy-6,8,4′-trimethoxyflavone, isoscutellarein, luteolin, and luteolin-7-O-glucoside, the methanol extract of the aerial parts of Stachys aegyptiaca yielded a new flavone identified as luteolin 3′,4′-dimethylether-7-O-β-D-glucoside on the basis of chemical and spectroscopic methods. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 444–445, September–October, 2007.     

Synthesis of new (+)-usnic acid derivatives with the flavone structure

Reactions of a chalcone derivative (synthesized earlier from usnic acid) with various oxidants (hydrogen peroxide, tert-butyl hydroperoxide, and dichlorodicyanobenzoquinone) gave new flavonols, dihydroflavonols, and flavones. Treatment of the starting chalcone with a nucleophilic reagent (NH₂NH₂·H₂O) afforded a dihydropyrazole-containing derivative.